MILFORD -- The man who brought uncounted millions into the city in the form of new development, and who also coined the motto "A small city with a big heart," will retire on Friday.

Bob Gregory served under three mayors as the city's director of community and economic development and also worked in a similar capacity before that as the head of the Chamber of Commerce. The city native was praised for his encyclopedic knowledge of the state and region, as well as knowing the ins and outs of attracting businesses and people to town.

"Bob was the consummate professional," said former mayor James L. Richetelli Jr. "He was born and raised in Milford and much of his career was at the Chamber of Commerce where he developed all kinds of relationships with the business community. He was also respected around the state as an expert in the field."

Richetelli said that Gregory was his "go-to" man whenever he had a question about some obscure fact or person in the city, a sentiment that was echoed by Mayor Benjamin G. Blake.

"After, his more than two decades as the economic development director and another two decades at the Chamber before that, he certainly knew the right person to talk to, to get things done," Blake said. "Certainly this is an institutional loss to the city."

Both Blake and Richetelli noted that it was Gregory who largely created the Milford Oyster Festival, a longtime annual event that continues to this day. But it wasn't all easy sledding.

"Not long after I was appointed back in '92, IBM announced that they were pulling out," Gregory recalled. "And then Bic Corporation left."

There were also weather issues, too, such as Storm Beth, the December 1992 nor'easter which like Tropical Storm Sandy, ravaged homes along the shorefront.

"I got involved in writing FEMA grants then, so it kind of added to my job description," he said.

Gregory, a member of the University of Connecticut class of 1959, signed on for a stint in the Army after leaving college and was honorably discharged with the rank of first lieutenant.

"When I went to UConn, there I was a wet-behind-the-ears 18-year-old kid from Milford, and my roommate was a 27-year-old Korean War vet in college on the GI Bill. I had a lot to learn," he said with a twinkle in his eye.

The Vietnam War broke out while he was in the Army.

"Fortunately, we didn't hear a lot about it," he said.

After leaving the Army, Gregory worked for a time at WNTY in Southington, 990 AM (now WXCT). He later found a job as head of the Southington Chamber of Commerce. After a few months there, he learned of the director's opening at the Milford Chamber, and he has worked in Milford ever since.